Antiplaque oral care compositions

ABSTRACT

The invention provides oral compositions including a safe and effective amount of a compound represented by the formula (I): 
     
       
         
         
             
             
         
       
     
     wherein R 1  and R 2  are independently selected from a hydrogen atom and an alkyl group and X′ is an anion, and n is an integer of 1 to 25; and (b) a surfactant.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a continuation-in-part of each of the following:U.S. patent application Ser. No. 10/601,473, U.S. patent applicationSer. No. 10/601,474, U.S. patent application Ser. No. 10/601,477, U.S.patent application Ser. No. 10/601,478, each filed Jun. 23, 2003; andU.S. patent application Ser. No. 10/875,059, filed Jun. 23, 2004; thecontents of each of which are incorporated herein by reference.

BACKGROUND OF THE INVENTION

Dental plaque is present to some degree in the form of a film onvirtually all dental surfaces. It is a byproduct of microbial growth,and comprises a dense microbial layer consisting of a mass ofmicroorganisms embedded in a polysaccharide matrix. It is reported thatplaque adheres firmly to dental surfaces and is removed only withdifficulty even through a rigorous brushing regimen. Moreover, plaquerapidly reforms on the tooth surface after it is removed. Plaque mayform on any part of the tooth surface, and is found particularly at thegingival margin, in cracks in the enamel, and on the surface of dentalcalculus. The problem associated with the formation of plaque on theteeth lies in the tendency of plaque to build up and eventually producegingivitis, periodontitis and other types of periodontal disease, aswell as dental caries, bad breath (halitosis) and dental calculus.

As plaque is formed by oral bacteria, a wide variety of antibacterialagents have been proposed to retard plaque formation and the oralinfections associated with plaque formation. For example, halogenatedhydroxydiprrehyl ether compounds such as triclosan are well known to theart for their antibacterial activity and have been used in oralcompositions to counter plaque formation by bacterial accumulation inthe oral cavity. However, these antibacterial agents which work toreduce plaque formation by temporary reduction in the population of oralbacteria have numerous disadvantages when incorporated into commercialproducts, including disadvantages stemming from production costs andlogistics, regulatory frameworks of various jurisdictions, stability ofcommercially acceptable formulations, etc.

Thus, there remains a need in the art for oral compositions that reduceor prevent plaque formation.

BRIEF SUMMARY OF THE INVENTION

The invention provides oral compositions including a safe and effectiveamount of a compound represented by the formula (I):

wherein R¹ and R² are independently selected from a hydrogen atom and analkyl group and X′ is an anion, and n is an integer of 1 to 25; and (b)a surfactant.

DETAILED DESCRIPTION OF THE INVENTION

The invention provides an oral care composition that contains thecompound represented by formula (I):

wherein R¹ and R² are independently selected from a hydrogen atom and analkyl group.

In various embodiments, R¹ is independently selected from an alkyl group1 to 25 carbon atoms, preferably 1 to 8 carbon atoms, most preferably 2,3, 4, 5, 6, or 7 carbon atoms. In various embodiments, R² is may be analkyl group having 1 to 50 carbon atoms, preferably 1 to 30 carbonatoms. The symbol “n” may be an integer of 1 to 10, preferably n is 3.

The group X′ may be an anion such that resultant ester salts is, forexample, a an inorganic acid salt such as a hydrochloride, or a sulfateor an organic salt such as acetate, tartarate or citrate.

In various embodiments, R²CO may be derived from a natural system mixedfatty acid residue such as coconut oil fatty acids, tallow fatty acids,or a mono-fatty acid residue such a lauroyl, myristyl, stearoyl and thelike, the lauroyl group being preferred.

Examples of antibacterial ester compounds preferred in the practice ofthe present invention are antibacterial ester compound of Formula (I)include N-alpha-cocoyl-L-arginine propyl ester, N alphastearoyl-L-arginine methyl ester, N steaoryl-L-arginine ethyl esterhydrochloride. The term “cocoyl” is an abbreviation for coconut oilfatty acid residue, and chloride salts of these ester compoundshereinafter being referred to as arginine derivative compounds. The saltof the arginine derivative compound, ethyl lauroyl arginine, may bepreferred for use in the practice of the present invention.

The oral composition of the invention includes a surfactant(s). Anyknown or to be developed in the art may be used, and the nature, ratioand content of the surfactant(s) used may be modified depending ion thespecific end product desired. Nonionic surfactants useful in the presentinvention include condensates of sorbitan esters of fatty acids withethylene oxide (polysorbates) such as sorbitan mono-oleate with fromabout 20 to about 60 moles of ethylene oxide and polysorbates.Zwitterionic surfactants that may be used include betaine surfactantsand those disclosed in U.S. Pat. No. 5,180,577, incorporated herein byreference, alkyldimethyl betaines, such as decyl betaine2-(N-decyl-N,N-dimethylammonio) acetate, cocobetaine or 2-(N-coc-N,N-dimethyl ammonio) acetate, myristyl betaine, palmityl betaine, lauryl,betaine, cetyl betaine, cetyl betaine, stearyl betaine, etc. Theamidobetaines are exemplified by cocoamidoethyl betaine, cocoamidopropylbetaine, laurmidopropyl betaine and the like.

Surfactants useful in the practice of the present invention includenonionic and zwitterionic surfactants. Suitable nonionic surfactantsuseful in the present invention includepoly(oxyethylene)-poly(oxypropyle-ne) block copolymers. Such copolymersare known commercially by the non-proprietary name of poloxamers, whichname is used in conjunction with a numeric suffix to designate theindividual identification of each copolymer.

Poloxamers may have varying contents of ethylene oxide and propyleneoxide which results in poloxamers which have a wide range of chemicalstructures and molecular weights.

The surfactants may be present in any amount. Preferred amounts areabout 0.1% to about 5% by weight or about 0.6% to about 2.0% by weight.

The composition may contain an abrasive, such as, for example, a silicacompound, perlite, pumice, calcium carbonate, calcium carbonate, polymerparticulates, dicalcium phosphate, alumina and precipitated silica. If asilica compound is selected, it may be one or more of the silicas knownor developed in the art for use in various consumer products, such as aprecipitated silica and/or a surface modified silica. The silica may bea silica coated with a glyceride of a fatty acid, for example,ricinoleic acid or the acids of castor oil.

Other silica abrasives that may be useful in the practice of the presentinvention include silica gels and precipitated amorphous silicas. Thesesilicas are colloidal particles having an average particle size rangingfrom about 3 microns to about 12 microns, and more preferably betweenabout 5 to about 10 microns and a pH range from 4 to 10 preferably 6 to9 when measured as a 5% by weight slurry.

Illustrative of silica abrasives useful in the practice of the presentinvention are marketed under the trade designation SYLODENT® XWA byDavison Chemical Division of W. R. Grace & Co., Baltimore, Md. 21203.SYLODENT® 650 XWA, a silica hydrogel composed of particles of colloidalsilica having a water content of 29% by weight averaging from about 7 toabout 10 microns in diameter.

Other abrasives used in the practice of the present invention mayinclude precipitated silicas having a mean particle size of up to about20 microns, such as ZEODENT® 115, marketed by J. M. Huber ChemicalsDivision, Havre de Grace, Md. 21078, or SYLODENT® 783 marketed byDavison Chemical Division of W. R. Grace & Company.

The silica abrasive materials may be used individually as the soleabrasive in preparing the dental composition of the present invention orin combination with other known dentifrice abrasives such as sodiummetaphosphate, dihydrated dicalcium phosphate, calcined alumina. Thetotal quantity of abrasive present in the dentifrice compositions of thepresent invention is at a level of from about 5% to about 60% by weight,preferably from about 10% to about 55% by weight when the dentifricecomposition is a toothpaste.

The ethoxylated hydrogenated castor oils used to precoat the silicacompounds prior to their incorporation into the dentifrice of thepresent invention are prepared by hydrogenating castor oil and treatingthe hydrogenated product with from about 10 to about 200 moles ofethylene glycol. These ethoxylated hydrogenated castor oils are known bythe non-proprietary name of PEG hydrogenated castor oils, in accordancewith dictionary of the Cosmetics, Toiletries and Fragrance Association,3rd Edition which name is used in conjunction with a numeric suffix todesignate the degree of ethoxylation of the hydrogenated castor oilproduct, i.e., the number of moles of ethylene oxide added to thehydrogenated castor oil product. Suitable PEG hydrogenated castor oilsinclude, PEG 16, 20, 25, 30, 40, 50, 60, 80, 100, and 200. In apreferred embodiment, the PEG 40 hydrogenated castor oil surfactant isCREMAPHOR RH40, a commercially available product from BASF-Wyandotte,Parsippany, N.J. Ethoxylated hydrogenated castor oil is coated on thesilica compounds used in the preparation of the compositions of thepresent invention at a castor oil to silica weight ratio of about 1:10to 1:2.

In some embodiments, it may be desirable to prepare a composition thatdoes not contain a monohydric alcohol.

The compositions of the invention may contain numerous and varied otheringredients and may be in different delivery forms. For example, thecomposition may take the form of a tablet, a suspension, and emulsion, alozenge, a confectionary, a chewing gum, a paste, a powder, a gel, asemi-solid stick, a spray, a film, a bead, a flake, a speckle, and aliquid.

If the composition is in the form of a film, it may contain a filmforming polymer, such as a water soluble film forming polymer and adispersible film-forming polymer. Such polymers may include anyknown/developed in the art. Suitable polymers may include polyvinylpyrrolidone, hydroxyethyl cellulose, hydroxypropyl methyl cellulose,hydroxyalkyl celluloses such as hydroxypropyl cellulose, carboxymethylcellulose, starch, polyvinyl alcohol, sodium alginate, alginate esters,guar gum, xanthan gum, gelatin, polyethylene oxide, polyethylene glycol,carrageenan, pullulan, locust bean gum as well as water dispersiblepolymers such as polyacrylates, carboxyvinyl copolymers, methylmethacrylate copolymers and polyacrylic acid. Specifially, one mayprefer a hydropropylmethyl cellulose polymer (29.1% methoxyl groups and9% hydroxyproxyl group substitution) having a viscosity of about 1 toabout 40 millipascal seconds (mPa.$) as determined as a 2% by weightaqueous solution of the HPMC at 20° C. using a Ubbelohde tubeviscometer.

Preferably the selected polymer has a viscosity of about 1 to about 50or 3 to about 20 mPa-s at 20° C.

The polymer may be incorporated in the film composition in amountsranging from about 10 to about 60% by weight and preferably about 15 toabout 40% by weight.

The composition may be in the form of a confectionary, such as a chewinggum or lozenge. If the form of a gum is desired, gum base materialssuitable for use in the practice of this invention are well known in theart and include natural or synthetic gum bases or mixtures thereofRepresentative natural gums or elastomers include chicle, naturalrubber, jelutong, balata, guttapercha, lechi caspi, sorva, guttakay,crown gum, perillo, or mixtures thereof Representative synthetic gums orelastomers include butadiene-styrene copolymers, polyisobutylene andisobutylene-isoprene copolymers.

The gum base may be incorporated in the gum at a concentration of about10 to about 40% by weight and preferably about 20 to about 35% byweight. If desired, plasticizing/softening agents commonly used inchewing gum compositions are suitable for use in this invention,including gelatin, waxes and mixtures thereof in, for example, amountsof 0.1 to 5% by weight. Suitable non-cariogenic gums include kappacarrageenan, carboxymethyl cellulose, hydroxyethyl cellulose and thelike.

If the form desired is a non-gum confenstionary, for example a lozengebead or tablet, one may include as a carrier such as a non-cariogenic,solid water-soluble polyhydric alcohol (polyol) (such as mannitol,xylitol, sorbitol, malitol), hydrogenated starch hydrozylate,hydrogenated glucose, hydrogenated disaccharides or hydrogenatedpolysaccharides, in an amount of about 85 to about 95% by weight of thetotal composition. Emulsifiers such as glycerin, and tabletinglubricants may be included Suitable lubricants for incorporation includevegetable oils such as coconut oil, magnesium stearate, aluminumstearate, talc, starch and Carbowax.

The lozenge, bead or tablet may optionally be coated with a materialsuch as waxes, shellac, carboxymethyl cellulose, polyethylene/maleicanhydride copolymer or kappa-carrageenan to, for example, furtherincrease the time it takes the tablet or lozenge to dissolve in themouth.

Other ingredients that may be included in the composition of theinvention include solid bases, sweeteners, sources of fluoride ions, ofzinc ion, of copper ions, of silver ions; zinc citrate, zinc gluconate,additional anti-caries or antiadhesion agents, anti-inflammatory agents,antiplaque agents, sweeteners, flavorants, rheology modifiers,antitartar agents, humectants, plasticizers, solvents, botanical agentsand herbs.

EXAMPLES Example I Mouthrinse

A mouthrinse of the present invention having a pH of 5.0 was prepared bydissolving in water each of the ingredients listed in Table I below withagitation in a glass mixing vessel.

TABLE I Ingredient Wt. % Ethyl lauroyl arginate HCl (ELAH) 0.1 Sorbitol10.0 Glycerin 10.0 Propylene glycol 7.0 Polysorbate 20 0.8Cocoamidopropyl betaine 0.8 Sodium saccharin 0.03 Flavor 0.10 Water Q.S.

After 9 months at room temperature, the ELAH concentration wasdetermined by Gas Chromatography-Mass Spectrometry to be unchanged at0.1% by weight.

Using this mouthrinse, a double blind randomized clinical study wasconducted in which 15 human subjects were asked to rinse for one minutewith either the mouthrinse in Example I or a matching placebo (i.e.,without ELAH) twice a day for 4 days while forgoing all othermaintenance oral hygiene. There was a statistically significantreduction of 11.6% in plaque using the mouth rinse of Table I. Theresults of the study are recorded in Table II below.

TABLE II Clinical efficacy of an alcohol-free mouthrinse Mouthrinse MeanQHI* (SD)** % Reduction relative to placebo Placebo 2.51 (0.30) — 0.1%ELAH 2.22 (0.22) 11.6** *QHI = Quitley & Hein Index (Art recognizedmeasure of plaque on teeth) **Standard Deviation **Significant at the95% confidence level

Example II Toothpaste

Toothpaste compositions containing ethyl lauroyl arginine HCL (ELAH)were prepared having the following ingredients:

TABLE III Composition (Wt. %) Ingredients A B C Polyethylene glycol 6003 3 3 PEG-40 castor oil 6 6 0 Hydroxyethyl cellulose 1.0 1.0 1.0 Xanthan0.2 0.2 0.2 Sodium saccharin 0.35 0.35 0.35 Sodium fluoride 0.243 0.2430.243 Sorbitol 40 40 40 Sodium hydroxide, 50% soln. 0.5 0.5 0.5 Titaniumdioxide 0.5 0.5 0.5 ELAH 0.5 0 0.5 ZEODENT ® 115 5 5 5 ZEODENT ® 165 2 22 SYLODENT ® XWA 650 15 15 15 Polysorbate 20 1 1 1 Cocomidopropylbetaine 1 1 1 Flavor 0.72 0.72 0.72 Water to make 100 100 100

The dentifrice “Composition A” was prepared by dispersing the sorbitolin the water in a conventional mixer under agitation. Into thedispersion was added the xanthan, PEG-40 castor oil, sodium fluoride,hydroxyethyl cellulose, and sodium saccharine. The resultant mixture wasagitated until a homogeneous gel phase was formed. Into the gel phasewas added TiO₂ and sodium hydroxide to adjust the pH to 6.5. Theseingredients were mixed until a homogenous phase was obtained. Themixture was then transferred to a high speed/vacuum mixer; wherein thePEG-40 castor oil coated silica compounds ZEODENT® 115, ZEODENT® 165,and SYLODENT® XWA 650 were added and the mixture mixed at high speed for25 minutes, under vacuum from about 30 mm Hg. Finally, polysorbate 20,cocoamidobetaine, flavor and ELAH were added to the mixture and mixedfor an additional 10 minutes. The resultant product was a homogenous,semisolid, extrudable paste or gel product.

For purposes of contrast, the procedure of the Example was repeated toprepare Composition B with the exception that ELAH was not included inthe dentifrice formula. A second comparative composition, Composition C,was also prepared following the procedure of the Example with theexception that neither silica abrasive ZEODENT® 115 (Composition A) orthe silica abrasive ZEODENT® 165 (Composition B) present in thedentifrice was coated with the PEG-40 castor oil.

The stability of the ELAH present in the prepared dentifrice compositionA, B, C was measured by titrating a 0.015% wt. solution of thedentifrice with a 0.005N solution of sodiym lauryl sulfate (SLS). Therecovery results are recorded in Table IV below.

TABLE IV Composition % Recovery ELAH A 87.1 B 3.0 C 7.5 ELAH (Palcebo)102.8

The antiplaque activity of Composition C was assessed using a flow cellmodel of the type disclosed in the Journal of Dental Research, vol.73(11), pp. 1748-1755 (1994). Pooled human saliva was used as thebacterial source and single crystal geranium prisms as the oral surfacemodel. Prior to exposure to bacteria, the surfaces were treated with a2:1 dentifrice water slurry and then rinsed with artificial saliva (1part porcine mucin 25 g/L, and 1 part saliva buffer solution) for 30minutes under 1 mL/min flow conditions.

Composition A was assessed for overall plaque inhibition versus thecomparative Composition B which did not contain ELAH, and Composition Cin which the silica abrasive and thickener were not precoated withPEG-40 castor oil. The compositions were simultaneously run in thesystem. The lower plaque score the more effective the antiplaque agent.The results recorded in Table V below show a significant reduction inplaque effected by Composition A when compared to comparativeCompositions B and C.

TABLE V Composition Plaque Index % reduction A 1.4237 17.5 B 1.7232 — C1.6705  3.2

The results recorded in Table V indicate that Composition A containingthe PEG-40 castor oil coated silica compounds was more effective inplaque reduction than composition C which the silica compounds were notcoated with the PEG-40 castor oil as well as Composition B which did notcontain ELAH.

Example III

A series of films containing varying amounts of the arginine derivativecompound they hydrochloride salt of ethyl lauroyl arginine designatedCompositions A, B and C were prepared by using the ingredients listed inTable VI below. In preparing the film, the hydroxylpropylmethylcellulose polymer ingredient (Methocel E5LV) and carrageenanas added at a temperature of 70° C. to 90° C., to half the amount oftotal deionized water used, and the solution stirred for 20 minutes at aslow speed using IKA Labortechnik Model RW2ODZMixer. The remainingamount of water maintained at room temperature (21° C.) was then addedand the mixing continued for 40 minutes. To this solution was added thecorn starch ingredient (Cerestar Polar Tex Instant 12640) and themixture stirred for an additional 20 minutes until the starch wascompletely dispersed and a homogenous mixture was formed. To thismixture was added sucralose and mixed for 10 minutes after which theemulsifier Tween 80 was added and mixed for an additional 5 minutes.Thereafter, flavor was thoroughly mixed for an additional 30 minutes toform a flurry emulsion to which as a final step the hydrochloride saltof ethyl lauroyl arginine HCL (ELAH) dispersed in canola oil was slowlyadded until evenly dispersed in the film ingredient slurry. The emulsionwas then cast on a polyethylene coated paper substrate and dried in aconvection oven at 110° C. to form a solid thin (30 to 60 μm thick)film.

For purposes of comparison, the procedure of Example III was repeated toprepare a film composition designated Composition D with the exceptionthat no ethyl lauroyl arginine HCL was incorporated in the filmcomposition.

TABLE VI Composition (Wt. %) Ingredients A B C D HPMC 41.0 41.0 38 41.0Carageenan 0.50 0.50 0.50 0.50 Corn Starch 19.0 19.0 17 19.0 Flavor 25.025.0 18 25.0 Tween 80 2.30 2.30 2.1 2.30 Canola oil 4.50 4.50 4.1 4.50Sucralose 1.4 1.4 1.3 1.4 Propylene glycol 1.25 6.25 11.5 0 ELAH 0.502.5 5.0 0 Water Q.S. Q.S. Q.S. Q.S.

The antiplaque activity of Compositions A, B, C and D was assessed usinga flow cell model of the type disclosed in the Journal of DentalResearch, vol. 73(11), pp. 1748-1755 (1994) using human saliva as thebacterial source and single crystal germanium prisms as the oral surfacemodel. After pretreatment of these surfaces with a precisely cut strip(10 mm×20 mm), they were rinsed with artificial saliva (1 part porcinemucin 25 g/L, and 1 part saliva buffer solution) prior to exposure tobacteria, and exposed to treatment in the flow cell. The plaque index ofthe deposits on the prisms was determined by infrared spectrophotometry.

Plaque Score

Compositions A, B and C were assessed for overall plaque inhibitionversus the comparative Composition D which did not contain anantibacterial agent which was simultaneously run in the system. Thelower the Plaque Index the more effective the antiplaque agent. Theresults recorded in Table VII below show a 30-40% reduction in plaqueeffected by Film Compositions A, B and C when compared to FolmComposition D.

TABLE VII Composition Plaque Index % reduction A 0.429 37.7 B 0.466 32.4C 0.486 29.6 D 0.690 —

Example IV

A second series of film compositions designated E and F were preparedfollowing the procedure of Example I, in which Composition E contained5% by weight (dry film) ELAH, Composition F contained 5% by weight (dryfilm) ELAH and 1.5% by weight (dry film) zinc gluconate. For purposes ofcomparison, film Composition G prepared in the same manner as Film A butwhich contained no ELAH and Film Composition H, a commercially availablebreath freshening film were tested for antiplaque efficacy in theartificial mouth test model. The tests were run in parallel underidentical conditions wherein 4 hydroxyapatitie discs (HAP) disks werecoated with pellicle for two hours followed by additional 2 hours ofbacteria attachment. The disks were mounted in a flow cell and 10 μmLsolution of film (containing 150 mg film) were then passed over thesurface of the disks for 1-2 minutes; water was passed over the disksfor 10 minutes to wash. The flow cell was then connected to theartificial mouth chemostat circulator and incubated for 8-12 hours. Theprocedure was repeated 4 times, and thereafter the HAP disks weredismounted and bacteria on the disks were detached. The bacteria werequantified by optical density readings. The results of this testprocedure are recorded in Table VIII below.

TABLE VIII Optical Density Film Composition Mean Standard Deviation %Reduction E 0.23 0.02 31.2 F 0.20 0.03 38.9 G 0.33 0.05 0 H 0.38 0.381.0

The results in Table VIII show that antibacterial films of the presentinvention (Films E, F) effect a significant reduction in antiplaqueformation when compared to films G, H that did not contain the argininederivative compound.

Example V

The procedure of Example IV was repeated in which a series of filmcompositions designated J, K were prepared following the procedure ofExample I in which Composition E contained 5% by weight (dry film) ELAH,Composition L contained 5% by weight (dry film) ELAH and 1.5% by weight(dry film) zinc gluconate. For purposes of comparison, Composition Mcontained 5% by weight (dry film) Triclosan, but no ELAH and CompositionH was a placebo containing no ELAH or antibacterial ester compound.

The antiplaque efficacy of the films was evaluated following theartificial mouth model described in Example IV. The results of thesetests are recorded in Table IX below.

TABLE IX Optical Density Film Composition Mean Standard Deviation %Reduction J 0.23 0.02 31.2 K 0.20 0.03 38.9 L 0.23 0.03 30.6 M 0.33 0.050.0

The results recorded in Table IX indicate that ELAH is at leasteffective as Triclosan in reducing plaque formation when delivered tothe oral cavity from a consumable film and that a combination of ELAHand a metal salt such as zinc gluconate provides antiplaque efficacysuperior to Triclosan.

Example VI

A series of film compositions designated Compositions N, P, Q wereprepared following the procedure of Example I, in which Composition Ncontained 0.50 by weight ELAH, Composition P contained 2.5% ELAH andComposition Q contained 5% by weight ELAH.

For purposes of comparison film Composition R was also preparedfollowing the procedure of Example I except that no ELAH wasincorporated in the film composition.

Film Compositions N, P, Q and R were evaluated for breath fresheningefficacy by an in-vitro volatile sulfur compound (VSC) reduction assay.In this assay a known amount of film is dissolved in 3.0 milliliters(ml) of saliva in a glass vial. After incubation at 37° C. overnight,the headspace of the solution is sampled and analyzed for the VSC. TheVSC assay results are presented in Table X below.

TABLE X VSC in the headspace Film Composition Baseline After 24 hoursVSC Reduction (%) N 27.3 23.90 12.5 O 27.3 18.36 32.8 Q 27.3 4.56 83.3 R27.3 25.61 6.3

The VSC assay results recorded in Table X demonstrate the increase inVSC reduction as the concentration of the antibacterial ester ELAH inthe film matrix is increased.

Example VII

TABLE XI Lozenge Ingredient Wt. % Saccharin 0.15 Magnesium Stearate 0.40Glycerin 1.0 Ethyl lauroyl arginine 0.5 Flavor 2.0 Sorbitol Q.S

Example VIII

TABLE XII Bead Ingredient Wt. % Gelatin 30 Flavor 45 Vegetable oil 22.5Aspartame 0.2 Ethyl lauroyl arginine 1 Food color 0.002 Flavor 2.0 Ethylalcohol 0.3 Water Q.S.

Example IX

TABLE XIII Tablet Ingredient Wt. % Starch coated dicalcium phosphate 40Cellulose 20 Glycerin 12 Sorbitol 17 Sodium saccharin 0.2 Flavor 1Lechithin 0.5 Ethyl lauroyl arginine 0.5 Water Q.S.

Example X

TABLE XIV Chewing Gum Ingredient Wt. % Gum base 25 Binder 10 Aspartame0.5 Ethyl lauroyl arginine 1 Flavor 2.0 Titanium dioxide 0.4Sorbitol/maltitol (50:50) Q.S.

1. An oral care composition comprising: (a) a safe and effective amountof a compound represented by the formula (I):

wherein R¹ and R² are independently selected from a hydrogen atom and analkyl group and X⁻ is an anion, and n is an integer of 1 to 25: (b) asurfactant; and (c) a silica compound coated with a fatty acid.
 2. Thecomposition of claim 1, wherein the composition is free of a monohydricalcohol.
 3. The composition of claim 1, wherein R¹ is an alkyl grouphaving 1 to 25 carbon atoms, R² is an alkyl group having 1 to 50 carbonatoms and n is an integer of 1 to
 10. 4. The composition of claim 1,wherein R¹ is an alkyl group having 1 to 8 carbon atoms, R² is an alkylgroup having 1 to 30 carbon atoms and wherein n is
 3. 5-8. (canceled) 9.The composition of claim 1, wherein X⁻ is selected from a hydrochlorideanion, a sulfate anion, an acetate anion, a tartarate anion, and acitrate anion.
 10. The composition of claim 1 wherein the compound isthe hydrochloride salt of ethyl lauroyl arginine.
 11. The composition ofclaim 1, wherein the compound is present at a concentration of about0.02% to about 2% by weight of the composition.
 12. The composition ofclaim 1, wherein the compound is present at a concentration of about0.05% to about 25% by weight of the composition.
 13. The composition ofclaim 1, wherein the surfactant is selected from a nonionic surfactantand a zwitterionic surfactant.
 14. The composition of claim 1, furthercomprising a polyhydric alcohol humectant.
 15. The composition of claim1, wherein the composition further comprises an uncoated abrasive. 16.The composition of claim 15, wherein the uncoated abrasive is selectedfrom a silica compound, perlite, pumice, calcium carbonate, polymerparticulates, and precipitated silica. 17-18. (canceled)
 19. Thecomposition of claim 1 having a form selected from a tablet, a lozenge,a confectionary, a chewing gum, a paste, a powder, a gel, a semi-solidstick, a spray, a film, a bead, a flake, a speckle, and a liquid. 20.The composition of claim 1, wherein the composition further comprises asolid base and a sweetener.
 21. The composition of claim 1, wherein thecomposition is in the form of a film and further comprises afilm-forming polymer selected from a water soluble film-forming polymerand a dispersible film-forming polymer.
 22. The composition of claim 21,wherein the polymer is selected from a hydroxyalkyl cellulose polymerand a hydroxymethylpropyl cellulose.
 23. The composition of claim 21,wherein the polymer is present in the composition in a concentration ofabout 10% to about 60% by weight of the composition.
 24. The compositionof claim 1, further comprising a metal salt.
 25. The composition ofclaim 1 claim 24, wherein the metal salt is selected zinc gluconate andzinc citrate.
 26. The composition of claim 1, wherein the fatty acid isselected from the group consisting of ricinoleic acid and stearic acid.